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CAS No. : | 136470-78-5 | MDL No. : | MFCD00903850 |
Formula : | C14H18N6O | Boiling Point : | - |
Linear Structure Formula : | C11H12N5ONC3H6 | InChI Key : | MCGSCOLBFJQGHM-SCZZXKLOSA-N |
M.W : | 286.33 | Pubchem ID : | 441300 |
Synonyms : |
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Chemical Name : | ((1S,4R)-4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol |
Signal Word: | Danger | Class: | N/A |
Precautionary Statements: | P501-P261-P202-P285-P201-P280-P272-P308+P313-P304+P341-P302+P352-P333+P313-P363-P405 | UN#: | N/A |
Hazard Statements: | H361-H317-H334-H341 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 25 - 30℃; | To a suspension of Abacavir free base (75 g, 261.9 mmol), 2-(tert-butoxy) acetic acid (41.54 g, 314.3 mmol) and DMAP (48 g, 392.9 mmol) in DCM (825 mL) was added EDC-HC1 (3 *25.11 g, 393 mmol) lot wise and the mixture was stirred for 2-3 hours at 25-30°C. Afterreaction completion, added 10percent ammonium chloride solution, separated the organic layer and concentrated under vacuum. Crude dissolved in toluene and washed with 15percent aqueous acetic acid, followed by water, 5percent aqueous sodium bicarbonate solution and finally 10percent aqueous sodium chloride solution. The organic layer was concentrated under vacuum, dissolved in DCM (150 mL) and slowly added n-heptane (450 mL). The suspension was stirred for 10-12 hours at25-30°C, followed by 5-6 hours at 0-5°C. The product was filtered, washed with n-heptane (150 mL) and dried under vacuum to yield ((iS, 4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9- yl) cyclopent-2-en-1-yl) methyl 2-(tert-butoxy) acetate as a white powder (yield 74percent).The purity by HPLC analysis was 99.3percent. ?H NMR (400 MHz, DMSO-d6): 7.60 (s, 1H), 7.27 (s, 1H), 6.08 (d, J= 5.2 Hz, 1H), 5.96 (d, J= 6.0 Hz, 1H), 5.81 (s, 2H), 5.42?5.41 (m,1H), 4.16-4.13 (m, 2H), 3.99 (d, J= 3.2 Hz, 2H), 3.11-3.08 (m, 1H), 3.11-3.08 (m, 1H), 2.69?2.65 (m, 1H,), 1.62? 1.58 (m, 1H), 1.12 (s, 9H), 0.65 ?0.57 (m, 4H). JR (KBr): v 3327, 3191,2973, 1764, 1648, 1610, 1487, 1265, and 1186 cm1. |